My friend Amy is a smart, attractive professional woman in her late 20s, who -- despite being just as cool in person as she is on paper -- is still unattached. Some friends recently set her up with a guy, and the circumstances of their first (and only) date were unique. They went on a road trip together. It ended disastrously, but thankfully for the rest of us, it was at least comically awkward -- and offered up a lesson in how not find a romantic partner.

The guy lives in another state. Her friends, another couple, had been telling the would-be daters about each other for some time. The guy, Kevin, eventually sent her a Facebook friend request, and the two corresponded. Eventually, they graduated to texting and spoke on the phone a few times. They seemed to have a lot in common, and he had a good sense of humor. Half-jokingly, he invited her to a concert in his hometown of Cincinnati. After mulling it over -- and much to his surprise -- she accepted.

The plan was this: Kevin would fly to Dallas-Fort Worth and the two would rent a car, and then drive to Ohio. Amy picked him up at the airport, and brought him to downtown Fort Worth to say hello to their mutual friends. Kevin was polite, but the conversation was a little stilted and awkward. Next the two headed for lunch. Amy noticed Kevin would just charge ahead of her, with no regard for crosswalks. She practically had to jog to keep up.

Amy hoped his awkward, distant behavior was just nerves or travel fatigue -- though she had to have known better. After sleeping at her place, in separate rooms, the two took off the next morning. Never on the entire trip did he ever try and touch her -- not even hand-holding or a touch on the shoulder. He continued to dart ahead of her everywhere they went. At a stop at Graceland, he took a lot of pictures, but none with her.

It quickly became clear to Amy that this was never going to be a romantic relationship, but she held out hope that maybe they could be friends. After a couple of days of driving and forced conversation, they arrived in Cincinnati. After the concert, the two met up with some friends of his at a club. He darted in ahead of her, and she lost him. She eventually found him, but he ignored her the rest of the night. He escorted her to the hotel that he had booked for her, but not to her room.

"I felt like an idiot," she said to me.

The next day and evening passed without much incident. The two visited a museum, and Amy sat in his guest bedroom watching episodes of Breaking Bad until she went to sleep. He apologized for being so awkward the previous evening but seemed to think that Amy was disappointed that nothing happened physically. He dropped her off at the airport the next morning, and the two haven't spoken since.

It's pretty clear Kevin is socially awkward -- when Amy told me the story, I diagnosed him as possibly having Aspberger's. But I also think Amy should shoulder some of the blame for her disastrous encounter. Long-distance relationships rarely work, setups rarely work and road trips can be relationship killers. She agreed to all three. I give her credit for daring, but she was being completely impractical. As for Kevin, it sounds like he just didn't like her, and he knew it from the get-go.

It just goes to show that you can't really get to know someone over the phone or online. Some lessons, unfortunately, you only learn the hard way. On the other hand, maybe you get to know someone a little too well during a 15-hour car ride.

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